More than three million children in the United States are currently enrolled in charter schools, with increasing enrollments despite strong evidence of academic gains. This historical analysis moves beyond a focus on academic outcomes and traces the success of the charter school movement, in part, to the foundational premise of restoring agency to educational stakeholders. State-mandated schooling was a counterintuitive feature of American policy that chafed against the founding ideals of the Republic and gradually engendered resentment among mostly white conservatives. Concurrently, in the aftermath of Brown, factions of African American policymakers began to look for equitable educational alternatives. The unlikely alliance of these two antithetical constituencies resulted in the creation of a unique—albeit fragile—coalition and the passing of the Milwaukee Parental Choice Program and paved the way for the nation’s inaugural charter school policy passed in Minnesota in 1991.